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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1615–o1616.
Published online 2010 June 9. doi:  10.1107/S1600536810020362
PMCID: PMC3006693

3′,4′-Dichloro­biphenyl-4-yl 2,2,2-trichloro­ethyl sulfate

Abstract

The four independent mol­ecules in the asymmetric unit of the title compound, C14H9Cl5O4S, are related by pseudo-inversion centres. The mol­ecules have Caromatic—O bond lengths ranging from 1.426 (10) to 1.449 (9) Å and biphenyl-4-yl sulfate ester bond lengths ranging from 1.563 (6) to 1.586 (6) Å, which is comparable to structurally related sulfuric acid diesters. The dihedral angles between the benzene rings range from 22.5 (4) to 29.1 (4)° and are significantly smaller than the calculated dihedral angle of 41.2°.

Related literature

For the structures of similar sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters, see: Li et al. (2008 [triangle], 2010a [triangle],b [triangle]). For a review of the structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005 [triangle]). For further discussion of dihedral angles in chlorinated biphenyl derivatives, see: Lehmler et al. (2002 [triangle]); Shaikh et al. (2008 [triangle]); Vyas et al. (2006 [triangle]). For additional background on polychlorinated biphenyls, see: Letcher et al. (2000 [triangle]); Robertson & Hansen (2001 [triangle]); Liu et al. (2004a [triangle],b [triangle]); Liu et al. (2006 [triangle], 2009 [triangle]); Sacco & James (2005 [triangle]); Tampal et al. (2002 [triangle]). For software used to caculate dihedral angles, see: Carpenter et al. (1980 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1615-scheme1.jpg

Experimental

Crystal data

  • C14H9Cl5O4S
  • M r = 450.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1615-efi1.jpg
  • a = 7.2491 (1) Å
  • b = 40.5988 (7) Å
  • c = 12.1145 (2) Å
  • β = 106.1551 (7)°
  • V = 3424.57 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.99 mm−1
  • T = 90 K
  • 0.40 × 0.34 × 0.18 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.658, T max = 0.843
  • 44794 measured reflections
  • 14652 independent reflections
  • 8149 reflections with I > 2σ(I)
  • R int = 0.110

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.156
  • S = 1.00
  • 14652 reflections
  • 769 parameters
  • 249 restraints
  • H-atom parameters constrained
  • Δρmax = 1.11 e Å−3
  • Δρmin = −0.59 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 6676 Friedel pairs
  • Flack parameter: 0.10 (9)

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97 and local procedures.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020362/lh5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020362/lh5052Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was supported by grants ES05605, ES013661 and ES017425 from the National Institute of Environmental Health Sciences, NIH.

supplementary crystallographic information

Comment

Hydroxylated polychlorinated biphenyls (PCBs) are an important class of metabolites of PCBs (Letcher et al., 2000) that can be further metabolized to PCB glucuronides (Tampal et al., 2002) or sulfates (Liu et al., 2006; Liu et al., 2009; Sacco & James, 2005). The chemical structure and toxicity of these glucuronide and sulfate metabolites are only poorly investigated, in part because authentic standards are not readily available or because of their limited chemical stability. Here we report the crystal structure of a 2,2,2-trichloroethyl-protected sulfate of 3',4'-dichloro-biphenyl-4-ol, an intermediate of the synthesis of the corresponding sulfate monoester.

The CAr—O (i.e. O1—C4) bond lengths of the title compound are 1.431 (10) Å (O1A—C4A), 1.426 (10) Å (O1B—C4B), 1.427 (10) Å (O1C—C4C) and 1.449 (9) Å (O1D—C4D), respectively. In related sulfuric acid diesters without chlorine substituents in the sulfated phenyl ring, the analogous CAr—O bond lengths were comparable and ranged from 1.426 (2) to 1.435 (5) Å (Li et al., 2010a,b; Li et al., 2008). A much shorter CAr—O bond length was observed in 2',3,5',5-tetrachloro-biphenyl-4-yl 2,2,2-trichloroethyl sulfate with 1.405 (4) Å (Li et al., 2010b). Similar to sulfate monoesters (Brandao et al., 2005), the differences in the CAr—O bond lengths of the sulfate diesters are due to a more positive partial charge on the C4 carbon atom in the presence of chlorine substituents, which results in a shorter CAr—O bond length.

The biphenyl-4-yl sulfate ester (i.e. S1—O1) bond lengths of the title compound were 1.571 (6) Å (S1A—O1A), 1.584 (6) Å (S1B—O1B), 1.586 (6) Å (S1C—O1C) and 1.563 (6) Å (S1D—O1D), respectively. These bond lengths are also comparable to related sulfuric acid diesters (Li et al., 2010a,b; Li et al., 2008), but shorter compared to 2',3,5',5-tetrachloro-biphenyl-4-yl 2,2,2-trichloroethyl sulfate, a sulfuric acid diester with two chlorine substituents in the sulfated phenyl ring (Li et al., 2010b). The differences in the biphenyl-4-yl sulfate ester bond lengths are also a due to the presence or absence of electron withdrawing chlorine substituents, which reduce the electron density on the oxygen atom and contribute to a longer and weaker bond in sulfate mono- and diesters with chlorine substituents in the sulfated phenyl ring (Brandao et al., 2005; Li et al., 2010b).

The four molecules in the asymmetyric unit are related by a pseudo-inversion center at (0.75056, 0.50005, 0.62549). Molecules with the A & B atom label suffixes are further related by a pseudo-inversion at (0.23935, 0.50071, 0.37554), while molecules C & D are related by a pseudo-inversion at (1.26176, 0.49939, 0.87544).

The dihedral angle Ar—Ar' between the phenyl rings of a PCB derivative determines its three dimensional structure and, thus, its affinity to cellular targets (Lehmler et al., 2002; Shaikh et al., 2008; Vyas et al., 2006). The solid state dihedral angles between the two phenyl rings of the title compound were 27.2 (4)°, 23.5 (4)°, 29.1 (4)° and 22.5 (4)°, respectively. The corresponding solid state dihedral angles of other sulfate diesters without ortho chlorine substituents range from 4.9 to 41.8° (Li et al., 2010a; Li et al., 2008). Typically, the dihedral angles of such sulfate diester derivatives are smaller than the calculated dihedral angle of 41.2° (calculated using semi-empirical SCF-MO calculations with an Austin Model 1 (AM1) Hamiltonian as implemented by the Spartan 02 package [Carpenter et al., 1980]). These deviations from the calculated dihedral angles are likely due to crystal packing effects, which allow the sulfate diester molecule to adopt an energetically unfavorable dihedral angle to maximize intermolecular interactions in the crystal. Overall, the differences between solid state and calculated dihedral angles indicate that the biphenyl moiety of biphenyl-4-yl sulfate ester has considerable conformational freedom in interacting with cellular target molecules.

Experimental

The title compound was synthesized from 3',4'-dichloro-biphenyl-4-ol by sulfation with 2,2,2-trichloroethyl sulfonyl chloride using 4-dimethylaminopyridine as catalyst (Li et al., 2008; Liu et al. 2004a,b). Crystals suitable for crystal structure analysis were obtained by slowly evaporating a methanolic solution of the title compound.

Refinement

H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained C—H distances of 0.99 Å (CH2), and 0.95 Å (CArH) with Uiso(H) values set to 1.2Ueq of the attached atom.

Figures

Fig. 1.
View of one of the four independent molecules of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C14H9Cl5O4SF(000) = 1808
Mr = 450.52Dx = 1.748 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 47065 reflections
a = 7.2491 (1) Åθ = 1.0–27.5°
b = 40.5988 (7) ŵ = 0.99 mm1
c = 12.1145 (2) ÅT = 90 K
β = 106.1551 (7)°Block, colourless
V = 3424.57 (9) Å30.40 × 0.34 × 0.18 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer14652 independent reflections
Radiation source: fine-focus sealed tube8149 reflections with I > 2σ(I)
graphiteRint = 0.110
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 1.8°
ω scans at fixed χ = 55°h = −9→9
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)k = −52→52
Tmin = 0.658, Tmax = 0.843l = 0→15
44794 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.156w = 1/[σ2(Fo2) + (0.0685P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
14652 reflectionsΔρmax = 1.11 e Å3
769 parametersΔρmin = −0.59 e Å3
249 restraintsAbsolute structure: Flack (1983), 6676 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.10 (9)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.There is a pseudo inversion at (0.75070 0.50000 0.62576), but it does seem as if the space group really is P21. This came as a great surprise because there seems to be no obvious reason why this structure would be non-centrosymmetric. All indications are that the crystals themselves are non even inversion twins because the Flack (and Hooft 'y') parameters are both zero within a couple of SUs. Although these SUs are a bit larger than the recommendation suggested by Flack. Further tests with various procedures in PLATON (including ADDSYM) suggest "No Obvious Spacegroup Change Needed/Suggested", but the checkCIF implementation of ADDSYM does suggest "ADDSYM Detects Additional (Pseudo) Symm. Elem··· m", but on inspection the structure does not seem to have any kind of mirror plane. Further, the checkCIF implementation of ADDSYM/MISSYM suggests "Potential lattice centering or halving", but again, on inspection of the model and the diffraction data this does not appear to be the case.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S1A0.0897 (3)0.41379 (5)0.3801 (2)0.0212 (6)
O1A0.2072 (8)0.38089 (14)0.4093 (5)0.0201 (14)
O2A0.2419 (9)0.44128 (15)0.4286 (6)0.0215 (14)
O3A0.0317 (9)0.41873 (16)0.2587 (6)0.0263 (15)
O4A−0.0441 (8)0.41263 (15)0.4467 (6)0.0284 (16)
Cl1A0.5435 (3)0.24939 (5)−0.10621 (17)0.0304 (5)
Cl2A0.8863 (3)0.28876 (5)−0.1569 (2)0.0305 (6)
Cl3A0.4320 (3)0.50544 (5)0.5117 (2)0.0244 (6)
Cl4A0.5427 (3)0.47314 (5)0.7332 (2)0.0261 (6)
Cl5A0.6711 (3)0.44744 (5)0.5439 (2)0.0227 (6)
C1A0.4851 (13)0.3429 (2)0.1757 (9)0.0197 (19)
C2A0.5790 (11)0.36492 (19)0.2620 (7)0.023 (2)
H2A0.70790.37110.26810.027*
C3A0.4877 (12)0.37792 (19)0.3385 (7)0.0238 (19)
H3A0.55290.39280.39690.029*
C4A0.3030 (13)0.3690 (2)0.3287 (8)0.020 (2)
C5A0.2038 (12)0.34682 (18)0.2459 (7)0.0267 (19)
H5A0.07510.34080.24100.032*
C6A0.2961 (11)0.33403 (19)0.1724 (7)0.0230 (18)
H6A0.23050.31850.11650.028*
C7A0.3002 (12)0.44536 (19)0.5532 (8)0.0217 (10)
H7A10.32920.42370.59150.026*
H7A20.19600.45590.57880.026*
C8A0.4790 (12)0.46710 (18)0.5830 (8)0.0180 (10)
C1'A0.5824 (11)0.32855 (19)0.0935 (8)0.0194 (10)
C2'A0.5326 (11)0.29847 (19)0.0421 (6)0.0220 (10)
H2'A0.43500.28590.06090.026*
C3'A0.6208 (11)0.28622 (17)−0.0356 (6)0.0191 (9)
C4'A0.7679 (10)0.30432 (19)−0.0626 (7)0.0207 (10)
C5'A0.8189 (10)0.33416 (18)−0.0107 (7)0.0239 (11)
H5'A0.92020.3463−0.02700.029*
C6'A0.7259 (10)0.34709 (18)0.0654 (7)0.0222 (11)
H6'A0.75910.36830.09810.027*
S1B0.4062 (3)0.59117 (5)0.3690 (2)0.0230 (6)
O1B0.2827 (8)0.62391 (15)0.3453 (5)0.0212 (14)
O2B0.2532 (9)0.56336 (14)0.3155 (6)0.0197 (14)
O3B0.4676 (9)0.58420 (16)0.4878 (6)0.0292 (16)
O4B0.5361 (9)0.59447 (15)0.3028 (6)0.0271 (16)
Cl1B−0.0381 (3)0.73774 (5)0.90518 (18)0.0349 (6)
Cl2B−0.4422 (3)0.70796 (5)0.9015 (2)0.0340 (6)
Cl3B0.0707 (3)0.49999 (5)0.2225 (2)0.0258 (6)
Cl4B−0.0582 (4)0.53617 (6)0.0088 (2)0.0300 (6)
Cl5B−0.1718 (3)0.55696 (6)0.2089 (2)0.0275 (6)
C1B−0.0147 (13)0.6568 (2)0.5751 (9)0.0200 (19)
C2B−0.0462 (11)0.62525 (19)0.5291 (7)0.0215 (19)
H2B−0.13360.61120.55230.026*
C3B0.0429 (12)0.6137 (2)0.4523 (7)0.025 (2)
H3B0.01340.59260.41830.030*
C4B0.1814 (13)0.6343 (2)0.4246 (8)0.0186 (19)
C5B0.2204 (12)0.66517 (18)0.4713 (7)0.025 (2)
H5B0.31600.67850.45360.030*
C6B0.1199 (10)0.67649 (19)0.5436 (7)0.0224 (19)
H6B0.14220.69830.57310.027*
C7B0.1908 (12)0.56185 (19)0.1911 (8)0.0216 (10)
H7B10.29340.55270.16080.026*
H7B20.15660.58410.15800.026*
C8B0.0133 (13)0.53908 (19)0.1617 (8)0.0214 (10)
C1'B−0.1193 (11)0.66870 (19)0.6604 (8)0.0186 (10)
C2'B−0.0398 (11)0.69443 (17)0.7376 (6)0.0211 (10)
H2'B0.08130.70360.73870.025*
C3'B−0.1394 (12)0.70619 (17)0.8115 (7)0.0217 (10)
C4'B−0.3189 (11)0.6936 (2)0.8076 (7)0.0230 (11)
C5'B−0.3956 (11)0.66792 (19)0.7326 (7)0.0264 (11)
H5'B−0.51610.65860.73210.032*
C6'B−0.2966 (10)0.65610 (18)0.6594 (7)0.0224 (11)
H6'B−0.35110.63900.60720.027*
S1C1.3915 (3)0.58721 (5)0.8798 (2)0.0214 (6)
O1C1.2647 (9)0.61955 (15)0.8500 (5)0.0242 (15)
O2C1.2418 (8)0.55900 (14)0.8285 (6)0.0177 (13)
O3C1.4484 (9)0.58174 (15)0.9986 (6)0.0258 (15)
O4C1.5231 (9)0.58960 (16)0.8136 (6)0.0276 (16)
Cl1C0.9555 (3)0.75553 (5)1.35532 (17)0.0298 (5)
Cl2C0.6170 (3)0.71937 (5)1.4213 (2)0.0291 (6)
Cl3C1.0490 (3)0.49568 (5)0.7412 (2)0.0263 (6)
Cl4C0.9415 (3)0.52908 (6)0.5218 (2)0.0272 (6)
Cl5C0.8154 (3)0.55435 (5)0.7123 (2)0.0234 (6)
C1C0.9952 (13)0.6580 (2)1.0860 (8)0.0180 (18)
C2C0.8978 (12)0.6360 (2)1.0020 (7)0.0213 (19)
H2C0.76860.63020.99670.026*
C3C0.9883 (11)0.6224 (2)0.9259 (8)0.021 (2)
H3C0.92250.60700.86950.025*
C4C1.1745 (13)0.6314 (2)0.9331 (9)0.020 (2)
C5C1.2746 (11)0.65297 (18)1.0156 (7)0.0226 (19)
H5C1.40250.65911.01890.027*
C6C1.1847 (11)0.66571 (18)1.0941 (7)0.0245 (19)
H6C1.25420.67981.15390.029*
C7C1.1868 (12)0.55543 (19)0.7048 (8)0.0217 (10)
H7C11.29000.54440.67950.026*
H7C21.16130.57720.66710.026*
C8C1.0047 (12)0.53442 (19)0.6746 (8)0.0180 (10)
C1'C0.9007 (11)0.6729 (2)1.1687 (8)0.0194 (10)
C2'C0.9571 (11)0.70446 (18)1.2150 (7)0.0220 (10)
H2'C1.05300.71631.19200.026*
C3'C0.8720 (11)0.71828 (17)1.2947 (7)0.0191 (9)
C4'C0.7265 (10)0.70184 (19)1.3256 (7)0.0207 (10)
C5'C0.6697 (10)0.67109 (18)1.2808 (7)0.0239 (11)
H5'C0.57050.65971.30220.029*
C6'C0.7582 (10)0.65668 (18)1.2039 (6)0.0222 (11)
H6'C0.71980.63531.17490.027*
S1D1.1226 (3)0.40890 (5)0.8723 (2)0.0231 (6)
O1D1.2492 (9)0.37714 (14)0.8970 (6)0.0249 (15)
O2D1.2695 (9)0.43669 (15)0.9271 (6)0.0236 (14)
O3D1.0666 (9)0.41554 (16)0.7527 (6)0.0258 (15)
O4D0.9884 (9)0.40510 (15)0.9376 (6)0.0302 (17)
Cl1D1.5275 (3)0.25787 (5)0.33982 (19)0.0384 (6)
Cl2D1.9395 (4)0.28238 (6)0.3372 (2)0.0377 (6)
Cl3D1.4471 (3)0.50056 (6)1.0258 (2)0.0277 (6)
Cl4D1.5717 (4)0.46324 (6)1.2378 (2)0.0313 (6)
Cl5D1.6925 (3)0.44383 (6)1.0375 (2)0.0271 (6)
C1D1.5371 (12)0.3415 (2)0.6623 (8)0.0188 (19)
C2D1.5793 (11)0.3726 (2)0.7139 (7)0.0188 (18)
H2D1.67480.38580.69540.023*
C3D1.4871 (12)0.3845 (2)0.7900 (7)0.025 (2)
H3D1.51910.40560.82440.030*
C4D1.3491 (13)0.3658 (2)0.8158 (8)0.020 (2)
C5D1.3035 (10)0.33494 (18)0.7725 (7)0.0214 (18)
H5D1.20960.32210.79410.026*
C6D1.3979 (11)0.32293 (19)0.6966 (7)0.0242 (19)
H6D1.36800.30140.66620.029*
C7D1.3283 (12)0.43822 (19)1.0533 (8)0.0216 (10)
H7D11.36130.41601.08660.026*
H7D21.22400.44741.08200.026*
C8D1.5031 (13)0.4606 (2)1.0844 (8)0.0214 (10)
C1'D1.6335 (11)0.32815 (19)0.5800 (8)0.0186 (10)
C2'D1.5501 (11)0.30334 (18)0.5052 (6)0.0211 (10)
H2'D1.42640.29560.50520.025*
C3'D1.6406 (12)0.28921 (18)0.4299 (7)0.0217 (10)
C4'D1.8203 (11)0.30051 (19)0.4282 (7)0.0230 (11)
C5'D1.9067 (11)0.32561 (18)0.5010 (7)0.0264 (11)
H5'D2.02920.33360.49950.032*
C6'D1.8147 (10)0.33916 (18)0.5761 (6)0.0224 (11)
H6'D1.87590.35630.62630.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0144 (12)0.0222 (12)0.0243 (15)0.0009 (9)0.0012 (11)−0.0047 (10)
O1A0.022 (3)0.018 (3)0.019 (4)0.003 (2)0.005 (3)−0.001 (2)
O2A0.019 (3)0.025 (3)0.017 (3)−0.004 (2)−0.001 (3)−0.003 (3)
O3A0.022 (4)0.033 (4)0.019 (3)0.009 (3)−0.003 (3)−0.007 (3)
O4A0.016 (3)0.037 (4)0.035 (4)−0.001 (3)0.011 (3)−0.014 (3)
Cl1A0.0348 (13)0.0293 (12)0.0293 (13)−0.0069 (9)0.0126 (10)−0.0087 (10)
Cl2A0.0346 (13)0.0305 (12)0.0323 (13)0.0078 (9)0.0188 (11)0.0069 (10)
Cl3A0.0275 (13)0.0194 (11)0.0251 (14)0.0000 (9)0.0055 (10)0.0018 (10)
Cl4A0.0261 (13)0.0303 (13)0.0211 (13)−0.0051 (9)0.0055 (10)−0.0025 (10)
Cl5A0.0165 (12)0.0257 (12)0.0257 (15)0.0004 (9)0.0056 (11)−0.0017 (10)
C1A0.020 (5)0.012 (4)0.026 (5)0.004 (3)0.005 (4)−0.001 (3)
C2A0.015 (4)0.023 (4)0.028 (5)−0.006 (3)0.002 (4)−0.001 (4)
C3A0.032 (4)0.013 (4)0.025 (5)−0.001 (3)0.005 (4)0.000 (3)
C4A0.023 (5)0.019 (4)0.017 (5)0.009 (3)0.006 (4)0.005 (3)
C5A0.023 (4)0.019 (4)0.037 (5)0.000 (3)0.005 (4)0.001 (4)
C6A0.023 (4)0.022 (4)0.020 (5)−0.004 (3)0.000 (4)0.000 (3)
C7A0.022 (2)0.021 (2)0.020 (2)−0.0052 (18)0.0028 (19)−0.0055 (19)
C8A0.011 (2)0.022 (2)0.019 (2)−0.0015 (17)0.0019 (18)−0.0006 (18)
C1'A0.015 (2)0.020 (2)0.022 (3)0.0018 (18)0.0032 (19)0.0026 (18)
C2'A0.020 (2)0.022 (2)0.026 (3)0.0031 (19)0.009 (2)0.0043 (19)
C3'A0.021 (2)0.015 (2)0.018 (2)−0.0054 (18)0.0011 (18)−0.0016 (18)
C4'A0.020 (2)0.017 (2)0.028 (3)0.0067 (18)0.011 (2)0.004 (2)
C5'A0.020 (3)0.020 (2)0.033 (3)0.0026 (19)0.011 (2)0.010 (2)
C6'A0.023 (3)0.017 (2)0.025 (3)−0.0019 (19)0.004 (2)0.002 (2)
S1B0.0190 (13)0.0205 (11)0.0275 (15)−0.0011 (9)0.0034 (11)−0.0024 (10)
O1B0.023 (3)0.021 (3)0.019 (4)0.001 (2)0.004 (3)0.000 (3)
O2B0.023 (3)0.019 (3)0.014 (3)−0.006 (2)0.001 (3)−0.001 (3)
O3B0.030 (4)0.027 (4)0.024 (4)0.001 (3)−0.003 (3)0.001 (3)
O4B0.019 (3)0.021 (3)0.043 (4)−0.006 (2)0.012 (3)−0.008 (3)
Cl1B0.0393 (13)0.0315 (12)0.0332 (14)−0.0022 (10)0.0089 (11)−0.0108 (10)
Cl2B0.0449 (15)0.0324 (12)0.0309 (14)0.0079 (10)0.0208 (11)0.0038 (11)
Cl3B0.0262 (13)0.0218 (11)0.0287 (14)−0.0015 (9)0.0061 (10)0.0000 (10)
Cl4B0.0325 (14)0.0342 (13)0.0203 (13)−0.0054 (10)0.0024 (11)−0.0041 (10)
Cl5B0.0193 (13)0.0335 (13)0.0289 (16)0.0020 (10)0.0052 (11)−0.0034 (11)
C1B0.017 (4)0.024 (4)0.017 (5)0.003 (3)0.002 (4)0.007 (3)
C2B0.014 (4)0.022 (4)0.028 (5)−0.004 (3)0.006 (4)0.000 (4)
C3B0.036 (5)0.017 (4)0.021 (5)−0.001 (3)0.008 (4)−0.001 (4)
C4B0.022 (5)0.018 (4)0.017 (5)0.006 (3)0.007 (4)0.003 (3)
C5B0.033 (5)0.018 (4)0.026 (5)−0.006 (3)0.010 (4)0.002 (4)
C6B0.022 (5)0.017 (4)0.024 (5)−0.003 (3)0.001 (4)−0.004 (4)
C7B0.023 (3)0.023 (2)0.018 (2)−0.0027 (19)0.0032 (19)0.0011 (19)
C8B0.020 (3)0.023 (2)0.020 (2)0.0023 (18)0.004 (2)−0.0017 (19)
C1'B0.015 (2)0.017 (2)0.021 (3)0.0037 (18)0.0005 (18)0.0009 (18)
C2'B0.023 (2)0.015 (2)0.024 (3)−0.0031 (18)0.005 (2)0.0013 (18)
C3'B0.028 (3)0.015 (2)0.020 (3)0.0018 (19)0.005 (2)0.0003 (19)
C4'B0.026 (3)0.025 (3)0.018 (3)0.009 (2)0.006 (2)0.005 (2)
C5'B0.023 (3)0.029 (3)0.027 (3)0.001 (2)0.007 (2)0.009 (2)
C6'B0.021 (2)0.021 (3)0.022 (3)−0.004 (2)0.002 (2)0.000 (2)
S1C0.0168 (12)0.0220 (12)0.0247 (15)−0.0005 (9)0.0047 (11)−0.0026 (10)
O1C0.026 (3)0.024 (3)0.022 (4)0.006 (2)0.005 (3)−0.002 (3)
O2C0.015 (3)0.020 (3)0.017 (3)0.000 (2)0.004 (3)0.001 (3)
O3C0.024 (4)0.024 (3)0.023 (3)0.000 (3)−0.004 (3)−0.004 (3)
O4C0.019 (3)0.034 (4)0.034 (4)−0.006 (3)0.014 (3)−0.004 (3)
Cl1C0.0302 (12)0.0263 (11)0.0381 (14)−0.0078 (9)0.0179 (11)−0.0122 (10)
Cl2C0.0332 (13)0.0271 (11)0.0329 (14)0.0021 (9)0.0191 (11)0.0018 (10)
Cl3C0.0246 (13)0.0213 (11)0.0334 (15)−0.0017 (9)0.0086 (11)−0.0008 (10)
Cl4C0.0261 (13)0.0366 (14)0.0185 (13)−0.0075 (10)0.0055 (10)−0.0055 (10)
Cl5C0.0182 (13)0.0247 (12)0.0269 (15)0.0012 (9)0.0056 (11)−0.0010 (11)
C1C0.015 (4)0.022 (4)0.014 (5)0.003 (3)−0.001 (3)0.007 (3)
C2C0.015 (4)0.024 (4)0.023 (5)−0.001 (3)0.002 (4)−0.001 (3)
C3C0.010 (4)0.023 (4)0.030 (5)−0.003 (3)0.004 (4)−0.007 (4)
C4C0.021 (4)0.016 (4)0.026 (5)−0.001 (3)0.012 (4)0.001 (3)
C5C0.014 (4)0.020 (4)0.032 (5)−0.003 (3)0.003 (4)−0.008 (4)
C6C0.025 (4)0.023 (4)0.028 (5)−0.001 (3)0.012 (4)−0.002 (4)
C7C0.022 (2)0.021 (2)0.020 (2)−0.0052 (18)0.0028 (19)−0.0055 (19)
C8C0.011 (2)0.022 (2)0.019 (2)−0.0015 (17)0.0019 (18)−0.0006 (18)
C1'C0.015 (2)0.020 (2)0.022 (3)0.0018 (18)0.0032 (19)0.0026 (18)
C2'C0.020 (2)0.022 (2)0.026 (3)0.0031 (19)0.009 (2)0.0043 (19)
C3'C0.021 (2)0.015 (2)0.018 (2)−0.0054 (18)0.0011 (18)−0.0016 (18)
C4'C0.020 (2)0.017 (2)0.028 (3)0.0067 (18)0.011 (2)0.004 (2)
C5'C0.020 (3)0.020 (2)0.033 (3)0.0026 (19)0.011 (2)0.010 (2)
C6'C0.023 (3)0.017 (2)0.025 (3)−0.0019 (19)0.004 (2)0.002 (2)
S1D0.0183 (12)0.0207 (11)0.0268 (15)−0.0013 (9)0.0003 (11)−0.0027 (10)
O1D0.035 (4)0.018 (3)0.026 (4)0.003 (2)0.016 (3)0.000 (3)
O2D0.024 (3)0.028 (3)0.017 (3)−0.003 (2)0.002 (3)−0.004 (3)
O3D0.020 (3)0.030 (4)0.022 (3)0.004 (3)−0.002 (3)0.000 (3)
O4D0.025 (4)0.033 (4)0.035 (4)−0.001 (3)0.012 (3)0.000 (3)
Cl1D0.0458 (14)0.0328 (13)0.0382 (15)−0.0103 (10)0.0146 (12)−0.0116 (11)
Cl2D0.0480 (15)0.0372 (13)0.0348 (14)0.0042 (11)0.0231 (12)0.0000 (11)
Cl3D0.0303 (13)0.0209 (11)0.0291 (14)0.0023 (9)0.0038 (11)−0.0007 (10)
Cl4D0.0328 (14)0.0374 (14)0.0209 (14)−0.0032 (10)0.0030 (11)−0.0035 (11)
Cl5D0.0212 (13)0.0306 (13)0.0284 (16)0.0038 (10)0.0053 (12)−0.0064 (11)
C1D0.015 (4)0.025 (4)0.013 (5)−0.001 (3)−0.003 (3)−0.002 (3)
C2D0.013 (4)0.029 (4)0.012 (4)−0.007 (3)−0.001 (3)0.000 (3)
C3D0.037 (5)0.014 (4)0.024 (5)−0.003 (3)0.007 (4)−0.003 (4)
C4D0.019 (5)0.027 (4)0.011 (5)0.001 (3)0.002 (4)0.000 (4)
C5D0.016 (4)0.023 (4)0.024 (5)0.008 (3)0.003 (3)0.005 (3)
C6D0.029 (5)0.017 (4)0.028 (5)−0.002 (3)0.010 (4)0.001 (4)
C7D0.023 (3)0.023 (2)0.018 (2)−0.0027 (19)0.0032 (19)0.0011 (19)
C8D0.020 (3)0.023 (2)0.020 (2)0.0023 (18)0.004 (2)−0.0017 (19)
C1'D0.015 (2)0.017 (2)0.021 (3)0.0037 (18)0.0005 (18)0.0009 (18)
C2'D0.023 (2)0.015 (2)0.024 (3)−0.0031 (18)0.005 (2)0.0013 (18)
C3'D0.028 (3)0.015 (2)0.020 (3)0.0018 (19)0.005 (2)0.0003 (19)
C4'D0.026 (3)0.025 (3)0.018 (3)0.009 (2)0.006 (2)0.005 (2)
C5'D0.023 (3)0.029 (3)0.027 (3)0.001 (2)0.007 (2)0.009 (2)
C6'D0.021 (2)0.021 (3)0.022 (3)−0.004 (2)0.002 (2)0.000 (2)

Geometric parameters (Å, °)

S1A—O4A1.425 (6)S1C—O3C1.399 (8)
S1A—O3A1.428 (7)S1C—O4C1.410 (6)
S1A—O2A1.564 (6)S1C—O2C1.581 (7)
S1A—O1A1.571 (6)S1C—O1C1.586 (6)
O1A—C4A1.431 (10)O1C—C4C1.427 (10)
O2A—C7A1.459 (11)O2C—C7C1.447 (11)
Cl1A—C3'A1.736 (7)Cl1C—C3'C1.716 (7)
Cl2A—C4'A1.729 (8)Cl2C—C4'C1.730 (8)
Cl3A—C8A1.767 (8)Cl3C—C8C1.756 (8)
Cl4A—C8A1.765 (10)Cl4C—C8C1.792 (9)
Cl5A—C8A1.780 (8)Cl5C—C8C1.759 (8)
C1A—C2A1.401 (12)C1C—C6C1.385 (11)
C1A—C6A1.406 (11)C1C—C2C1.391 (12)
C1A—C1'A1.490 (11)C1C—C1'C1.490 (12)
C2A—C3A1.385 (11)C2C—C3C1.385 (11)
C2A—H2A0.9500C2C—H2C0.9500
C3A—C4A1.360 (11)C3C—C4C1.378 (11)
C3A—H3A0.9500C3C—H3C0.9500
C4A—C5A1.389 (12)C4C—C5C1.375 (12)
C5A—C6A1.358 (10)C5C—C6C1.394 (10)
C5A—H5A0.9500C5C—H5C0.9500
C6A—H6A0.9500C6C—H6C0.9500
C7A—C8A1.527 (11)C7C—C8C1.528 (11)
C7A—H7A10.9900C7C—H7C10.9900
C7A—H7A20.9900C7C—H7C20.9900
C1'A—C2'A1.372 (11)C1'C—C6'C1.388 (10)
C1'A—C6'A1.400 (10)C1'C—C2'C1.413 (11)
C2'A—C3'A1.370 (10)C2'C—C3'C1.399 (10)
C2'A—H2'A0.9500C2'C—H2'C0.9500
C3'A—C4'A1.407 (10)C3'C—C4'C1.385 (10)
C4'A—C5'A1.368 (10)C4'C—C5'C1.378 (10)
C5'A—C6'A1.387 (10)C5'C—C6'C1.399 (10)
C5'A—H5'A0.9500C5'C—H5'C0.9500
C6'A—H6'A0.9500C6'C—H6'C0.9500
S1B—O4B1.403 (6)S1D—O3D1.417 (7)
S1B—O3B1.411 (8)S1D—O4D1.423 (6)
S1B—O1B1.584 (6)S1D—O1D1.563 (6)
S1B—O2B1.589 (6)S1D—O2D1.567 (7)
O1B—C4B1.426 (10)O1D—C4D1.449 (9)
O2B—C7B1.449 (11)O2D—C7D1.469 (11)
Cl1B—C3'B1.733 (8)Cl1D—C3'D1.727 (8)
Cl2B—C4'B1.731 (8)Cl2D—C4'D1.741 (8)
Cl3B—C8B1.750 (9)Cl3D—C8D1.774 (8)
Cl4B—C8B1.782 (10)Cl4D—C8D1.788 (10)
Cl5B—C8B1.756 (9)Cl5D—C8D1.761 (9)
C1B—C2B1.392 (12)C1D—C2D1.407 (11)
C1B—C6B1.393 (11)C1D—C6D1.411 (11)
C1B—C1'B1.520 (12)C1D—C1'D1.471 (11)
C2B—C3B1.354 (10)C2D—C3D1.368 (11)
C2B—H2B0.9500C2D—H2D0.9500
C3B—C4B1.416 (11)C3D—C4D1.360 (11)
C3B—H3B0.9500C3D—H3D0.9500
C4B—C5B1.372 (11)C4D—C5D1.363 (11)
C5B—C6B1.365 (10)C5D—C6D1.380 (10)
C5B—H5B0.9500C5D—H5D0.9500
C6B—H6B0.9500C6D—H6D0.9500
C7B—C8B1.543 (12)C7D—C8D1.518 (12)
C7B—H7B10.9900C7D—H7D10.9900
C7B—H7B20.9900C7D—H7D20.9900
C1'B—C6'B1.381 (10)C1'D—C2'D1.376 (11)
C1'B—C2'B1.413 (11)C1'D—C6'D1.401 (10)
C2'B—C3'B1.382 (10)C2'D—C3'D1.388 (10)
C2'B—H2'B0.9500C2'D—H2'D0.9500
C3'B—C4'B1.387 (10)C3'D—C4'D1.387 (10)
C4'B—C5'B1.393 (10)C4'D—C5'D1.379 (11)
C5'B—C6'B1.373 (10)C5'D—C6'D1.383 (10)
C5'B—H5'B0.9500C5'D—H5'D0.9500
C6'B—H6'B0.9500C6'D—H6'D0.9500
O4A—S1A—O3A122.5 (4)O3C—S1C—O4C122.9 (4)
O4A—S1A—O2A109.4 (4)O3C—S1C—O2C105.2 (4)
O3A—S1A—O2A105.1 (4)O4C—S1C—O2C109.0 (4)
O4A—S1A—O1A104.9 (4)O3C—S1C—O1C110.6 (4)
O3A—S1A—O1A109.7 (4)O4C—S1C—O1C104.7 (4)
O2A—S1A—O1A103.9 (3)O2C—S1C—O1C102.7 (3)
C4A—O1A—S1A118.0 (6)C4C—O1C—S1C117.9 (6)
C7A—O2A—S1A116.1 (5)C7C—O2C—S1C116.2 (5)
C2A—C1A—C6A116.9 (8)C6C—C1C—C2C119.2 (8)
C2A—C1A—C1'A121.8 (7)C6C—C1C—C1'C119.5 (8)
C6A—C1A—C1'A121.3 (8)C2C—C1C—C1'C121.2 (7)
C3A—C2A—C1A121.3 (8)C3C—C2C—C1C120.3 (8)
C3A—C2A—H2A119.3C3C—C2C—H2C119.8
C1A—C2A—H2A119.3C1C—C2C—H2C119.8
C4A—C3A—C2A118.8 (8)C4C—C3C—C2C119.3 (8)
C4A—C3A—H3A120.6C4C—C3C—H3C120.3
C2A—C3A—H3A120.6C2C—C3C—H3C120.3
C3A—C4A—C5A122.4 (8)C5C—C4C—C3C121.6 (8)
C3A—C4A—O1A120.2 (8)C5C—C4C—O1C118.3 (7)
C5A—C4A—O1A117.3 (8)C3C—C4C—O1C120.0 (8)
C6A—C5A—C4A118.1 (8)C4C—C5C—C6C118.7 (7)
C6A—C5A—H5A121.0C4C—C5C—H5C120.6
C4A—C5A—H5A121.0C6C—C5C—H5C120.6
C5A—C6A—C1A122.5 (8)C1C—C6C—C5C120.7 (8)
C5A—C6A—H6A118.7C1C—C6C—H6C119.7
C1A—C6A—H6A118.7C5C—C6C—H6C119.7
O2A—C7A—C8A107.0 (7)O2C—C7C—C8C106.0 (7)
O2A—C7A—H7A1110.3O2C—C7C—H7C1110.5
C8A—C7A—H7A1110.3C8C—C7C—H7C1110.5
O2A—C7A—H7A2110.3O2C—C7C—H7C2110.5
C8A—C7A—H7A2110.3C8C—C7C—H7C2110.5
H7A1—C7A—H7A2108.6H7C1—C7C—H7C2108.7
C7A—C8A—Cl4A106.6 (6)C7C—C8C—Cl3C110.8 (6)
C7A—C8A—Cl3A111.0 (6)C7C—C8C—Cl5C111.4 (6)
Cl4A—C8A—Cl3A109.9 (4)Cl3C—C8C—Cl5C110.4 (5)
C7A—C8A—Cl5A110.7 (5)C7C—C8C—Cl4C105.7 (6)
Cl4A—C8A—Cl5A109.7 (5)Cl3C—C8C—Cl4C109.1 (4)
Cl3A—C8A—Cl5A108.9 (5)Cl5C—C8C—Cl4C109.3 (5)
C2'A—C1'A—C6'A119.2 (7)C6'C—C1'C—C2'C117.7 (7)
C2'A—C1'A—C1A122.5 (7)C6'C—C1'C—C1C122.4 (7)
C6'A—C1'A—C1A118.3 (7)C2'C—C1'C—C1C119.9 (7)
C3'A—C2'A—C1'A121.4 (7)C3'C—C2'C—C1'C120.2 (7)
C3'A—C2'A—H2'A119.3C3'C—C2'C—H2'C119.9
C1'A—C2'A—H2'A119.3C1'C—C2'C—H2'C119.9
C2'A—C3'A—C4'A120.0 (7)C4'C—C3'C—C2'C120.5 (7)
C2'A—C3'A—Cl1A120.2 (6)C4'C—C3'C—Cl1C120.9 (6)
C4'A—C3'A—Cl1A119.8 (6)C2'C—C3'C—Cl1C118.5 (6)
C5'A—C4'A—C3'A118.7 (7)C5'C—C4'C—C3'C119.8 (7)
C5'A—C4'A—Cl2A120.5 (6)C5'C—C4'C—Cl2C119.6 (6)
C3'A—C4'A—Cl2A120.8 (6)C3'C—C4'C—Cl2C120.6 (6)
C4'A—C5'A—C6'A121.4 (7)C4'C—C5'C—C6'C119.9 (7)
C4'A—C5'A—H5'A119.3C4'C—C5'C—H5'C120.0
C6'A—C5'A—H5'A119.3C6'C—C5'C—H5'C120.0
C5'A—C6'A—C1'A119.3 (7)C1'C—C6'C—C5'C121.7 (7)
C5'A—C6'A—H6'A120.4C1'C—C6'C—H6'C119.2
C1'A—C6'A—H6'A120.4C5'C—C6'C—H6'C119.2
O4B—S1B—O3B122.1 (4)O3D—S1D—O4D122.9 (4)
O4B—S1B—O1B104.6 (4)O3D—S1D—O1D109.8 (4)
O3B—S1B—O1B110.8 (4)O4D—S1D—O1D105.1 (4)
O4B—S1B—O2B109.8 (4)O3D—S1D—O2D105.3 (4)
O3B—S1B—O2B105.1 (4)O4D—S1D—O2D109.3 (4)
O1B—S1B—O2B103.1 (3)O1D—S1D—O2D102.7 (4)
C4B—O1B—S1B119.8 (6)C4D—O1D—S1D120.7 (6)
C7B—O2B—S1B115.8 (5)C7D—O2D—S1D116.0 (5)
C2B—C1B—C6B117.8 (8)C2D—C1D—C6D115.7 (7)
C2B—C1B—C1'B120.5 (7)C2D—C1D—C1'D123.1 (7)
C6B—C1B—C1'B121.7 (8)C6D—C1D—C1'D121.1 (7)
C3B—C2B—C1B122.5 (8)C3D—C2D—C1D122.0 (8)
C3B—C2B—H2B118.8C3D—C2D—H2D119.0
C1B—C2B—H2B118.8C1D—C2D—H2D119.0
C2B—C3B—C4B117.7 (8)C4D—C3D—C2D119.1 (8)
C2B—C3B—H3B121.2C4D—C3D—H3D120.5
C4B—C3B—H3B121.2C2D—C3D—H3D120.5
C5B—C4B—C3B121.2 (8)C3D—C4D—C5D122.7 (8)
C5B—C4B—O1B117.5 (8)C3D—C4D—O1D121.1 (8)
C3B—C4B—O1B121.2 (8)C5D—C4D—O1D116.1 (7)
C6B—C5B—C4B119.1 (8)C4D—C5D—C6D118.0 (8)
C6B—C5B—H5B120.4C4D—C5D—H5D121.0
C4B—C5B—H5B120.4C6D—C5D—H5D121.0
C5B—C6B—C1B121.5 (8)C5D—C6D—C1D122.4 (7)
C5B—C6B—H6B119.2C5D—C6D—H6D118.8
C1B—C6B—H6B119.2C1D—C6D—H6D118.8
O2B—C7B—C8B105.3 (7)O2D—C7D—C8D105.4 (7)
O2B—C7B—H7B1110.7O2D—C7D—H7D1110.7
C8B—C7B—H7B1110.7C8D—C7D—H7D1110.7
O2B—C7B—H7B2110.7O2D—C7D—H7D2110.7
C8B—C7B—H7B2110.7C8D—C7D—H7D2110.7
H7B1—C7B—H7B2108.8H7D1—C7D—H7D2108.8
C7B—C8B—Cl3B111.1 (6)C7D—C8D—Cl5D111.2 (6)
C7B—C8B—Cl5B109.9 (6)C7D—C8D—Cl3D111.4 (6)
Cl3B—C8B—Cl5B110.6 (5)Cl5D—C8D—Cl3D109.6 (5)
C7B—C8B—Cl4B105.2 (6)C7D—C8D—Cl4D105.4 (6)
Cl3B—C8B—Cl4B110.1 (5)Cl5D—C8D—Cl4D110.0 (5)
Cl5B—C8B—Cl4B109.8 (5)Cl3D—C8D—Cl4D109.1 (5)
C6'B—C1'B—C2'B119.1 (7)C2'D—C1'D—C6'D117.1 (7)
C6'B—C1'B—C1B121.1 (7)C2'D—C1'D—C1D120.7 (7)
C2'B—C1'B—C1B119.7 (7)C6'D—C1'D—C1D122.2 (7)
C3'B—C2'B—C1'B119.6 (7)C1'D—C2'D—C3'D122.3 (7)
C3'B—C2'B—H2'B120.2C1'D—C2'D—H2'D118.9
C1'B—C2'B—H2'B120.2C3'D—C2'D—H2'D118.9
C2'B—C3'B—C4'B120.3 (7)C4'D—C3'D—C2'D119.4 (7)
C2'B—C3'B—Cl1B118.5 (6)C4'D—C3'D—Cl1D121.1 (6)
C4'B—C3'B—Cl1B121.1 (6)C2'D—C3'D—Cl1D119.5 (6)
C3'B—C4'B—C5'B119.9 (7)C5'D—C4'D—C3'D119.8 (7)
C3'B—C4'B—Cl2B120.3 (6)C5'D—C4'D—Cl2D120.0 (6)
C5'B—C4'B—Cl2B119.7 (6)C3'D—C4'D—Cl2D120.2 (6)
C6'B—C5'B—C4'B119.8 (7)C4'D—C5'D—C6'D119.9 (7)
C6'B—C5'B—H5'B120.1C4'D—C5'D—H5'D120.1
C4'B—C5'B—H5'B120.1C6'D—C5'D—H5'D120.1
C5'B—C6'B—C1'B121.2 (7)C5'D—C6'D—C1'D121.6 (7)
C5'B—C6'B—H6'B119.4C5'D—C6'D—H6'D119.2
C1'B—C6'B—H6'B119.4C1'D—C6'D—H6'D119.2
O4A—S1A—O1A—C4A158.0 (6)O3C—S1C—O1C—C4C−20.6 (7)
O3A—S1A—O1A—C4A24.7 (7)O4C—S1C—O1C—C4C−154.9 (6)
O2A—S1A—O1A—C4A−87.2 (7)O2C—S1C—O1C—C4C91.3 (7)
O4A—S1A—O2A—C7A36.5 (7)O3C—S1C—O2C—C7C−169.1 (6)
O3A—S1A—O2A—C7A169.7 (6)O4C—S1C—O2C—C7C−35.6 (7)
O1A—S1A—O2A—C7A−75.1 (6)O1C—S1C—O2C—C7C75.1 (6)
C6A—C1A—C2A—C3A−1.5 (12)C6C—C1C—C2C—C3C−1.3 (13)
C1'A—C1A—C2A—C3A−179.5 (8)C1'C—C1C—C2C—C3C−179.9 (8)
C1A—C2A—C3A—C4A−0.2 (12)C1C—C2C—C3C—C4C−1.1 (13)
C2A—C3A—C4A—C5A1.2 (13)C2C—C3C—C4C—C5C1.4 (14)
C2A—C3A—C4A—O1A177.4 (7)C2C—C3C—C4C—O1C−175.2 (8)
S1A—O1A—C4A—C3A91.2 (9)S1C—O1C—C4C—C5C89.0 (9)
S1A—O1A—C4A—C5A−92.4 (8)S1C—O1C—C4C—C3C−94.3 (9)
C3A—C4A—C5A—C6A−0.5 (13)C3C—C4C—C5C—C6C0.7 (14)
O1A—C4A—C5A—C6A−176.8 (7)O1C—C4C—C5C—C6C177.4 (7)
C4A—C5A—C6A—C1A−1.3 (13)C2C—C1C—C6C—C5C3.4 (13)
C2A—C1A—C6A—C5A2.2 (13)C1'C—C1C—C6C—C5C−177.9 (8)
C1'A—C1A—C6A—C5A−179.7 (8)C4C—C5C—C6C—C1C−3.1 (13)
S1A—O2A—C7A—C8A167.0 (5)S1C—O2C—C7C—C8C−164.1 (5)
O2A—C7A—C8A—Cl4A177.8 (5)O2C—C7C—C8C—Cl3C−60.2 (7)
O2A—C7A—C8A—Cl3A58.1 (7)O2C—C7C—C8C—Cl5C63.1 (8)
O2A—C7A—C8A—Cl5A−62.9 (7)O2C—C7C—C8C—Cl4C−178.3 (5)
C2A—C1A—C1'A—C2'A152.5 (8)C6C—C1C—C1'C—C6'C−148.8 (8)
C6A—C1A—C1'A—C2'A−25.4 (13)C2C—C1C—C1'C—C6'C29.8 (13)
C2A—C1A—C1'A—C6'A−29.5 (12)C6C—C1C—C1'C—C2'C30.5 (12)
C6A—C1A—C1'A—C6'A152.5 (8)C2C—C1C—C1'C—C2'C−150.9 (8)
C6'A—C1'A—C2'A—C3'A0.2 (12)C6'C—C1'C—C2'C—C3'C0.8 (12)
C1A—C1'A—C2'A—C3'A178.2 (8)C1C—C1'C—C2'C—C3'C−178.6 (8)
C1'A—C2'A—C3'A—C4'A1.1 (12)C1'C—C2'C—C3'C—C4'C−2.6 (12)
C1'A—C2'A—C3'A—Cl1A−175.7 (7)C1'C—C2'C—C3'C—Cl1C176.0 (6)
C2'A—C3'A—C4'A—C5'A−0.5 (12)C2'C—C3'C—C4'C—C5'C2.4 (12)
Cl1A—C3'A—C4'A—C5'A176.3 (6)Cl1C—C3'C—C4'C—C5'C−176.2 (6)
C2'A—C3'A—C4'A—Cl2A177.9 (6)C2'C—C3'C—C4'C—Cl2C−178.3 (6)
Cl1A—C3'A—C4'A—Cl2A−5.3 (10)Cl1C—C3'C—C4'C—Cl2C3.0 (10)
C3'A—C4'A—C5'A—C6'A−1.5 (12)C3'C—C4'C—C5'C—C6'C−0.4 (12)
Cl2A—C4'A—C5'A—C6'A−179.9 (6)Cl2C—C4'C—C5'C—C6'C−179.7 (6)
C4'A—C5'A—C6'A—C1'A2.9 (12)C2'C—C1'C—C6'C—C5'C1.2 (12)
C2'A—C1'A—C6'A—C5'A−2.2 (12)C1C—C1'C—C6'C—C5'C−179.4 (8)
C1A—C1'A—C6'A—C5'A179.8 (8)C4'C—C5'C—C6'C—C1'C−1.4 (12)
O4B—S1B—O1B—C4B−159.3 (7)O3D—S1D—O1D—C4D21.9 (8)
O3B—S1B—O1B—C4B−26.0 (8)O4D—S1D—O1D—C4D155.9 (7)
O2B—S1B—O1B—C4B85.9 (7)O2D—S1D—O1D—C4D−89.7 (7)
O4B—S1B—O2B—C7B−37.4 (7)O3D—S1D—O2D—C7D171.3 (6)
O3B—S1B—O2B—C7B−170.4 (6)O4D—S1D—O2D—C7D37.4 (7)
O1B—S1B—O2B—C7B73.5 (6)O1D—S1D—O2D—C7D−73.8 (6)
C6B—C1B—C2B—C3B−2.6 (13)C6D—C1D—C2D—C3D−1.8 (12)
C1'B—C1B—C2B—C3B179.6 (8)C1'D—C1D—C2D—C3D179.8 (8)
C1B—C2B—C3B—C4B4.0 (13)C1D—C2D—C3D—C4D−0.6 (13)
C2B—C3B—C4B—C5B−1.8 (13)C2D—C3D—C4D—C5D2.8 (14)
C2B—C3B—C4B—O1B179.5 (7)C2D—C3D—C4D—O1D179.2 (7)
S1B—O1B—C4B—C5B123.2 (8)S1D—O1D—C4D—C3D62.7 (11)
S1B—O1B—C4B—C3B−58.1 (11)S1D—O1D—C4D—C5D−120.7 (8)
C3B—C4B—C5B—C6B−1.6 (13)C3D—C4D—C5D—C6D−2.3 (14)
O1B—C4B—C5B—C6B177.1 (8)O1D—C4D—C5D—C6D−178.8 (7)
C4B—C5B—C6B—C1B3.0 (13)C4D—C5D—C6D—C1D−0.4 (12)
C2B—C1B—C6B—C5B−1.0 (13)C2D—C1D—C6D—C5D2.4 (12)
C1'B—C1B—C6B—C5B176.8 (8)C1'D—C1D—C6D—C5D−179.2 (8)
S1B—O2B—C7B—C8B−167.3 (5)S1D—O2D—C7D—C8D166.1 (5)
O2B—C7B—C8B—Cl3B−59.0 (7)O2D—C7D—C8D—Cl5D−62.1 (7)
O2B—C7B—C8B—Cl5B63.8 (7)O2D—C7D—C8D—Cl3D60.5 (7)
O2B—C7B—C8B—Cl4B−178.1 (5)O2D—C7D—C8D—Cl4D178.7 (5)
C2B—C1B—C1'B—C6'B−27.4 (13)C2D—C1D—C1'D—C2'D−159.1 (8)
C6B—C1B—C1'B—C6'B154.9 (8)C6D—C1D—C1'D—C2'D22.6 (13)
C2B—C1B—C1'B—C2'B156.4 (8)C2D—C1D—C1'D—C6'D22.8 (13)
C6B—C1B—C1'B—C2'B−21.3 (13)C6D—C1D—C1'D—C6'D−155.4 (8)
C6'B—C1'B—C2'B—C3'B0.8 (12)C6'D—C1'D—C2'D—C3'D0.9 (12)
C1B—C1'B—C2'B—C3'B177.1 (7)C1D—C1'D—C2'D—C3'D−177.2 (8)
C1'B—C2'B—C3'B—C4'B−2.0 (12)C1'D—C2'D—C3'D—C4'D−0.7 (12)
C1'B—C2'B—C3'B—Cl1B180.0 (6)C1'D—C2'D—C3'D—Cl1D179.3 (6)
C2'B—C3'B—C4'B—C5'B2.9 (12)C2'D—C3'D—C4'D—C5'D−0.1 (12)
Cl1B—C3'B—C4'B—C5'B−179.1 (6)Cl1D—C3'D—C4'D—C5'D179.9 (6)
C2'B—C3'B—C4'B—Cl2B179.1 (6)C2'D—C3'D—C4'D—Cl2D178.2 (6)
Cl1B—C3'B—C4'B—Cl2B−2.9 (10)Cl1D—C3'D—C4'D—Cl2D−1.8 (10)
C3'B—C4'B—C5'B—C6'B−2.7 (12)C3'D—C4'D—C5'D—C6'D0.7 (12)
Cl2B—C4'B—C5'B—C6'B−178.9 (6)Cl2D—C4'D—C5'D—C6'D−177.7 (6)
C4'B—C5'B—C6'B—C1'B1.5 (12)C4'D—C5'D—C6'D—C1'D−0.4 (12)
C2'B—C1'B—C6'B—C5'B−0.6 (12)C2'D—C1'D—C6'D—C5'D−0.3 (12)
C1B—C1'B—C6'B—C5'B−176.8 (8)C1D—C1'D—C6'D—C5'D177.7 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5052).

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